Sodium hydride → HCID 21201817, compound

HRID 1979317Notes

Reaction equation

HRID 1979317 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([C:13]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])[CH2:4][CH:3]1[NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].[H-].[Na+].Br[CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>O1CCCC1>[C:39]([O:38][C:36]([CH2:35][N:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([C:13]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:14])[CH2:4][CH:3]([NH:21][C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23])[C:2]1=[O:1])=[O:37])([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 21201688HCID 21201688, compound

Product 1

HCID 21201817HCID 21201817, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, 2-oxo-3-benzyloxycarbonylamino-5-cyclohexylcarbonyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (800 mg) was added to a suspension of 60% sodium hydride (152 mg) in tetrahydrofuran (50 ml), the mixture was stirred at room temperature for one hour. Subsequently, tert-butyl bromoacetate (390 mg) was added and stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, Water was added to the residue and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodiun sulfate, and the mixture was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 640 mg of the title compound (Yield: 63%).

Workup

  1. temperatureUnder ice-cooling
  2. stirringstirred at room temperature for one hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure, Water
  4. additionwas added to the residue
  5. extractionextracted with methylene chloride
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodiun sulfate
  8. customthe mixture was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-67d150bf4f104da0afb7fde038e61f83
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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